CA2542519A1 - Heat-stable diketopyrrolopyrrole pigment mixtures - Google Patents
Heat-stable diketopyrrolopyrrole pigment mixtures Download PDFInfo
- Publication number
- CA2542519A1 CA2542519A1 CA002542519A CA2542519A CA2542519A1 CA 2542519 A1 CA2542519 A1 CA 2542519A1 CA 002542519 A CA002542519 A CA 002542519A CA 2542519 A CA2542519 A CA 2542519A CA 2542519 A1 CA2542519 A1 CA 2542519A1
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- printing
- radical
- diketopyrrolopyrrole pigment
- diketopyrrolopyrrole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 205
- 239000000049 pigment Substances 0.000 title claims abstract description 161
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title claims abstract description 121
- -1 heteroaromatic nitrile Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 50
- 238000002360 preparation method Methods 0.000 claims abstract description 47
- 239000002537 cosmetic Substances 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 150000003900 succinic acid esters Chemical class 0.000 claims abstract description 4
- 238000007639 printing Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000976 ink Substances 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 23
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 22
- 239000004033 plastic Substances 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 17
- 229920003023 plastic Polymers 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 239000001384 succinic acid Substances 0.000 claims description 16
- 239000001993 wax Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 239000002480 mineral oil Substances 0.000 claims description 7
- 239000006071 cream Substances 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 239000002674 ointment Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 238000010023 transfer printing Methods 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 238000007641 inkjet printing Methods 0.000 claims description 3
- 238000005034 decoration Methods 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000002372 labelling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000007645 offset printing Methods 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 238000007650 screen-printing Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000011368 organic material Substances 0.000 abstract description 25
- 238000004040 coloring Methods 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 43
- 150000002148 esters Chemical class 0.000 description 22
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 20
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000001035 drying Methods 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 12
- 239000003086 colorant Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 239000004166 Lanolin Substances 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229940039717 lanolin Drugs 0.000 description 8
- 235000019388 lanolin Nutrition 0.000 description 8
- WSRJSKMFEHWCGL-UHFFFAOYSA-N 4-octadecylsulfanylbenzonitrile Chemical compound CCCCCCCCCCCCCCCCCCSC1=CC=C(C#N)C=C1 WSRJSKMFEHWCGL-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920001887 crystalline plastic Polymers 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 230000005588 protonation Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
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- 230000005855 radiation Effects 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 241001237961 Amanita rubescens Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Cosmetics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| CH01817/03 | 2003-10-23 | ||
| CH18172003 | 2003-10-23 | ||
| PCT/EP2004/052426 WO2005040284A1 (en) | 2003-10-23 | 2004-10-04 | Heat-stable diketopyrrolopyrrole pigment mixtures |
Publications (1)
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| CA2542519A1 true CA2542519A1 (en) | 2005-05-06 |
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| CA002542519A Abandoned CA2542519A1 (en) | 2003-10-23 | 2004-10-04 | Heat-stable diketopyrrolopyrrole pigment mixtures |
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| EP (1) | EP1675916B1 (enExample) |
| JP (1) | JP4994845B2 (enExample) |
| KR (1) | KR101120937B1 (enExample) |
| CN (1) | CN100439453C (enExample) |
| AU (1) | AU2004284235A1 (enExample) |
| BR (1) | BRPI0415831A (enExample) |
| CA (1) | CA2542519A1 (enExample) |
| MX (1) | MXPA06004377A (enExample) |
| TW (1) | TW200519114A (enExample) |
| WO (1) | WO2005040284A1 (enExample) |
| ZA (1) | ZA200602373B (enExample) |
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| DE602006014231D1 (de) * | 2005-02-22 | 2010-06-24 | Dainichiseika Color Chem | Diketopyrrolopyrrole-Pigmentdispergatoren und ihre Verwendung |
| DE102006007621A1 (de) * | 2006-02-18 | 2007-08-23 | Clariant International Limited | Diketopyrrolopyrrol-Pigmente mit erhöhten Echtheiten und Verfahren zu deren Herstellung |
| JP4144655B2 (ja) * | 2006-10-06 | 2008-09-03 | 東洋インキ製造株式会社 | α型ジケトピロロピロール顔料、それを用いた着色組成物、および赤色着色膜 |
| DE102007008140A1 (de) * | 2007-02-19 | 2008-08-21 | Clariant International Ltd. | Diketopyrrolopyrrol-Mischkristalle mit hoher Transparenz |
| JPWO2009081930A1 (ja) * | 2007-12-26 | 2011-05-06 | 東洋インキ製造株式会社 | 赤色カラーフィルター用顔料組成物、その製造方法、及びそれを用いた着色組成物、及びカラーフィルター |
| US8273269B2 (en) * | 2008-05-28 | 2012-09-25 | Basf Se | Red colour filter composition |
| EP2316890A1 (en) * | 2009-11-03 | 2011-05-04 | Agfa-Gevaert | Preparing and dispersing surface-modified colour pigments |
| US9021491B2 (en) * | 2010-03-15 | 2015-04-28 | International Business Machines Corporation | Dual mode reader writer lock |
| KR101920285B1 (ko) | 2011-01-28 | 2018-11-21 | 토요잉크Sc홀딩스주식회사 | 컬러필터용 디케토피롤로피롤계 안료 조성물, 컬러필터용 착색 조성물 및 컬러필터 |
| US20120276030A1 (en) * | 2011-04-29 | 2012-11-01 | Garden Art Innovations, Llc | Cosmetic composition |
| GB201200184D0 (en) | 2012-01-06 | 2012-02-22 | Johnson Matthey Plc | Tracers and method of marking liquids |
| US9440430B2 (en) | 2012-03-26 | 2016-09-13 | Canon Kabushiki Kaisha | Image recording method |
| US9340008B2 (en) * | 2012-03-26 | 2016-05-17 | Canon Kabushiki Kaisha | Image recording method |
| US9415581B2 (en) | 2012-03-26 | 2016-08-16 | Canon Kabushiki Kaisha | Image recording method |
| JP6229833B2 (ja) | 2013-10-03 | 2017-11-15 | セイコーエプソン株式会社 | 水性顔料分散液及びそれを含有する水性インク組成物 |
| JP6315172B2 (ja) | 2014-01-06 | 2018-04-25 | セイコーエプソン株式会社 | 卑金属顔料水性分散液および水性インク組成物 |
| JP6315174B2 (ja) | 2014-01-27 | 2018-04-25 | セイコーエプソン株式会社 | 卑金属顔料、卑金属顔料水性分散液および水性インク組成物 |
| US9353333B1 (en) | 2014-12-18 | 2016-05-31 | AS Innovations LLC | Laundry additive and drum treatment |
| CN104892979B (zh) * | 2014-12-31 | 2019-01-15 | 先尼科化工（上海）有限公司 | 在塑料中具有抗翘曲性能的颜料组合物 |
| CN108239421A (zh) * | 2017-12-25 | 2018-07-03 | 先尼科化工（上海）有限公司 | 一种具有高耐候性橙色二酮吡咯并吡咯颜料及其制备方法 |
| CN112313290B (zh) * | 2018-06-25 | 2022-11-04 | 太阳化学有限公司 | 滤色器用红色颜料组合物 |
| WO2021166859A1 (ja) * | 2020-02-20 | 2021-08-26 | 富士フイルム株式会社 | 着色組成物、膜、赤色画素、カラーフィルタ、固体撮像素子、画像表示装置およびキット |
| WO2024101179A1 (ja) * | 2022-11-10 | 2024-05-16 | Dic株式会社 | ジケトピロロピロール化合物 |
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| US457949A (en) | 1891-08-18 | Scaffold-bracket | ||
| DE3366011D1 (en) | 1982-05-17 | 1986-10-16 | Ciba Geigy Ag | Preparation of pyrrolo-(3,4-c) pyrroles |
| CS236794B2 (cs) * | 1982-05-17 | 1985-05-15 | Ciba Geigy Ag | Způsob přípravy l,4-diketopyrrolo[3,4-c]pyrrolu |
| DE3584138D1 (de) | 1984-11-07 | 1991-10-24 | Ciba Geigy Ag | Pigmentmischungen. |
| US4880472A (en) | 1987-06-16 | 1989-11-14 | Ciba-Geigy Corporation | Organic pigments coated with metal oxides |
| US4791204A (en) | 1985-11-26 | 1988-12-13 | Ciba-Geigy Corporation | 1,4-diketopyrrolo[3,4-c]pyrrole pigments |
| US4783540A (en) | 1986-08-07 | 1988-11-08 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrrols |
| US4889562A (en) | 1987-06-16 | 1989-12-26 | Ciba-Geigy Corporation | Organic pigments coated with crosslinked ethyl cellulose |
| US4808230A (en) | 1987-06-16 | 1989-02-28 | Ciba-Geigy Corporation | Organic pigments coated with metal oxides fixed with ethyl cellulose |
| JP2507810B2 (ja) * | 1989-07-13 | 1996-06-19 | 東洋インキ製造株式会社 | 顔料分散剤，顔料組成物，塗料および印刷インキ |
| EP0430875A3 (en) | 1989-11-28 | 1992-08-05 | Ciba-Geigy Ag | Water-based coating materials containing specific modified organic pigments |
| KR0143777B1 (ko) | 1989-11-28 | 1998-07-01 | 월터 클리웨인, 한스-피터 위트린 | 디케토피롤로피롤을 기재로 하는 물질의 조성물 |
| DE69109057T2 (de) | 1990-11-08 | 1995-09-21 | Ciba Geigy Ag | Pyrazol enthaltende Pigmentderivate. |
| US5145524A (en) | 1991-02-20 | 1992-09-08 | Ciba-Geigy Corporation | Surface modified pigment compositions |
| EP0511165B1 (de) | 1991-04-26 | 1996-08-14 | Ciba-Geigy Ag | Neue Diketopyrrolopyrrolverbindungen |
| CH685162A5 (de) | 1991-05-07 | 1995-04-13 | Ciba Geigy Ag | Pigmentzusammensetzungen. |
| US5679148A (en) | 1993-01-12 | 1997-10-21 | Ciba-Geigy Corporation | Pigment compositions of a diketopyrrolopyrrole and an aminoalkyl acrylate resin |
| EP0611252B1 (de) | 1993-02-09 | 1996-04-17 | Ciba-Geigy Ag | Mit Silanen beschichtete organische Pigmente |
| TW372244B (en) * | 1993-07-29 | 1999-10-21 | Ciba Sc Holding Ag | Process for producing novel finely divided highly transparent diketopyrrolopyrrole pigments |
| US5434452A (en) * | 1993-11-01 | 1995-07-18 | Motorola, Inc. | Z-axis compliant mechanical IC wiring substrate and method for making the same |
| DE59409613D1 (de) | 1993-12-01 | 2001-01-25 | Ciba Sc Holding Ag | Pigmentzusammensetzung aus modifiziertem Diketopyrrolopyrrol und Aminoalkylacrylatharz |
| DE59409309D1 (de) | 1993-12-22 | 2000-05-31 | Ciba Sc Holding Ag | Mit Zirkonium oder Titan-Phosphatkomplexen beschichtete organische Pigmente |
| DE59508226D1 (de) | 1994-12-15 | 2000-05-31 | Ciba Sc Holding Ag | Mit Metallphosphatkomplexen und Aminen beschichtete organische Pigmente |
| EP0748851B1 (de) | 1995-06-15 | 2001-05-09 | Ciba SC Holding AG | Pigmentzusammensetzungen aus Diketopyrrolopyrrolen |
| US5579949A (en) * | 1995-10-02 | 1996-12-03 | Dykes; Scott H. | Insulative "C" shaped sleeve for beverage cup |
| EP0790281B1 (en) | 1996-02-13 | 2001-12-05 | Ciba SC Holding AG | Pigment compositions |
| US5785750A (en) | 1996-09-26 | 1998-07-28 | Ciba Specialty Chemicals Corporation | 1,4-diketo-3,6-diarylpyrolo 3,4-c! pyrrole |
| US5786487A (en) * | 1996-09-26 | 1998-07-28 | Ciba Specialty Chemicals Corporation | 1,4-diketo-3,6-diarylpyrolo 3,4-C!pyrrole pigment derivatives |
| DE59804631D1 (de) | 1997-05-06 | 2002-08-08 | Ciba Sc Holding Ag | Diketopyrrolopyrrolzusammensetzungen |
| WO1998056859A1 (en) * | 1997-06-09 | 1998-12-17 | Ciba Specialty Chemicals Holding Inc. | Colorant blends containing a salt-forming azo pigment and a 1,4-diketo-3, 6-diarylpyrrolo(3,4-c)pyrolle |
| EP0952183B1 (de) * | 1998-04-22 | 2005-02-23 | Ciba SC Holding AG | Verzugsfreie Pigmentzusammensetzungen enthaltend Diaryl-diketopyrrolo 3,4c pyrrole |
| AU754087B2 (en) | 1998-04-22 | 2002-11-07 | Ciba Specialty Chemicals Holding Inc. | Preparation of alkylthio- and/or arylthio-substituted diketo-diaryl-pyrrolopyrroles |
| AU2094100A (en) | 1998-12-08 | 2000-06-26 | Ciba Specialty Chemicals Holding Inc. | Cosmetic preparations containing organic pigments from the class of pyrrolo-(3,4-c)-pyrroles |
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| FR2792526B1 (fr) * | 1999-04-22 | 2001-07-27 | Oreal | Composition cosmetique, notamment de maquillage, contenant un pigment derive de pyrrolopyrrole |
| JP4139063B2 (ja) * | 1999-10-28 | 2008-08-27 | オリヱント化学工業株式会社 | 筆記具インキ用油性赤色顔料分散液、および油性赤色顔料筆記具インキ |
| US20010015154A1 (en) * | 2000-01-27 | 2001-08-23 | Roman Lenz | Ternary pigment compositions |
| FR2814672B1 (fr) * | 2000-10-03 | 2003-03-21 | Oreal | Composition cosmetique a phase continue lipophile comprenant un pigment goniochromatique multicouche et son utilisation en maquillage |
| US7081540B2 (en) * | 2001-04-24 | 2006-07-25 | Ciba Specialty Chemicals Corporation | Pigment compositions and pigmented water-based coating materials |
| JP2003057425A (ja) * | 2001-08-08 | 2003-02-26 | Toyo Ink Mfg Co Ltd | カラーフィルタ用顔料、その製造方法、およびそれを用いたカラーフィルタ用着色組成物 |
| CN1553913B (zh) * | 2001-09-11 | 2011-10-05 | 西巴特殊化学品控股有限公司 | 吡咯并[3,4-c]吡咯的直接制备方法 |
| KR20050026958A (ko) * | 2002-07-17 | 2005-03-16 | 시바 스페셜티 케미칼스 홀딩 인크. | 디케토피롤로피롤 안료를 포함하는 고분자량 중합체 물질 |
| DE10235573A1 (de) | 2002-08-03 | 2004-02-12 | Clariant Gmbh | Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolpigmenten zum verzugsfreien Pigmentieren von teilkristallinen Kunststoffen |
| WO2004076457A1 (en) * | 2003-02-27 | 2004-09-10 | Mca Technologies Gmbh | Solvent-free process for the preparation of pyrrolo (3,4c) pyrrole compounds |
-
2004
- 2004-10-04 MX MXPA06004377A patent/MXPA06004377A/es unknown
- 2004-10-04 EP EP04791138.3A patent/EP1675916B1/en not_active Expired - Lifetime
- 2004-10-04 JP JP2006536078A patent/JP4994845B2/ja not_active Expired - Fee Related
- 2004-10-04 WO PCT/EP2004/052426 patent/WO2005040284A1/en not_active Ceased
- 2004-10-04 US US10/576,703 patent/US7417154B2/en not_active Expired - Lifetime
- 2004-10-04 AU AU2004284235A patent/AU2004284235A1/en not_active Abandoned
- 2004-10-04 BR BRPI0415831-8A patent/BRPI0415831A/pt not_active Application Discontinuation
- 2004-10-04 CA CA002542519A patent/CA2542519A1/en not_active Abandoned
- 2004-10-04 CN CNB2004800312968A patent/CN100439453C/zh not_active Expired - Lifetime
- 2004-10-22 TW TW093132176A patent/TW200519114A/zh unknown
-
2006
- 2006-03-23 ZA ZA200602373A patent/ZA200602373B/xx unknown
- 2006-05-22 KR KR1020067009946A patent/KR101120937B1/ko not_active Expired - Lifetime
-
2008
- 2008-07-17 US US12/218,904 patent/US7786313B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200602373B (en) | 2007-08-29 |
| CN100439453C (zh) | 2008-12-03 |
| KR101120937B1 (ko) | 2012-03-05 |
| CN1871309A (zh) | 2006-11-29 |
| AU2004284235A1 (en) | 2005-05-06 |
| EP1675916A1 (en) | 2006-07-05 |
| US7786313B2 (en) | 2010-08-31 |
| US7417154B2 (en) | 2008-08-26 |
| EP1675916B1 (en) | 2013-12-11 |
| JP2007514798A (ja) | 2007-06-07 |
| TW200519114A (en) | 2005-06-16 |
| US20070028807A1 (en) | 2007-02-08 |
| US20080287689A1 (en) | 2008-11-20 |
| BRPI0415831A (pt) | 2007-01-02 |
| JP4994845B2 (ja) | 2012-08-08 |
| MXPA06004377A (es) | 2006-06-14 |
| KR20060123181A (ko) | 2006-12-01 |
| WO2005040284A1 (en) | 2005-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |